And yet I feel like a bad parent because we don't have the resources to enroll him for all the activities his friends do. One event particularly stands out from my own childhood. I tried out for the wrestling team and when I brought the paperwork home my mom said I couldn't, we didn't have health insurance.
I wouldn't wish that on anyone. Being good at something and then being told you can't because you don't have the right paperwork.
Children are not identical to adults, and treating them like they should be free to make all of their own decisions at 5 years of age would be negligent.
But they are like adults in many ways that we tend to ignore - they may not have a great conception of which things can hurt them how badly, but they have a sense of dignity, and they have a sense of independence. They want to make decisions for themselves, and they need to interact with adults that treat them as a rational peer to whatever degree that is possible.
Give them what freedoms you can, and respect them enough to explain the real reasons for the rules you impose. Sometimes you may find that they aren't very good ones at all, when you try to explain them - when that happens, admit that it wasn't a good rule, and work out a better one with them.
That's not accurate. Kids are little people. Ignorant of many things, but they're little people. My wife reads these 'how to raise your kids' posts and books and crap, and all it does is make her feel as if she is a terrible parent because he wasn't signing at 10 months and isn't using full sentences at 12. She feels guilt that he may be behind other kids already, because he's not doing things that these posts and books suggest (and are mostly ridiculous).
Let kids be kids, let them climb trees and ride bikes and be alone. But, spend a lot of time with them and have them watch how you treat people, what you say about people and how you interact with the world. Take him/her with you when you work on the yard, just have them help by carrying rocks around. Take him/her to the store to get the fuel filter you're fighting right now. Talk to them as if they're capable and they'll be capable. Have boundaries that are firm, but reasonable.
And always, always remember that you can say whatever you want about their character being great, or their traits being great, but if you show malice and spite, they'll be malicious and spiteful as well.